N,N-Dimethylaniline → HCID 57682852, compound
Reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[C:10]([CH3:17])([CH3:16])[CH2:9][CH2:8]2)C=C.O.C(OCC)(=O)C.CN(C)[C:27]1[CH:32]=CC=C[CH:28]=1>>[CH2:32]([C:6]1[C:5]([OH:4])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10]([CH3:16])([CH3:17])[C:11]2=[O:15])[CH:27]=[CH2:28]Participants
Procedure
1.69 g of 6-(allyloxy)-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one was dissolved in 10 ml of N,N-dimethylaniline, and the obtained mixture was heated to reflux under nitrogen atmosphere for 7 hours. The reaction solution was cooled to a room temperature. Water and ethyl acetate were added to the reaction solution, so as to obtain an organic layer. The obtained organic layer was successively washed with 5 N hydrochloric acid (3 times), water (4 times), and a saturated sodium chloride solution. The resultant product was then dried over anhydrous sodium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. Hexane was added to the residue, and the precipitate was then collected by filtration, so as to obtain 1.06 g of the subject compound.
Workup
- temperaturethe obtained mixture was heated
- temperatureto reflux under nitrogen atmosphere for 7 hours
- customso as to obtain an organic layer
- washThe obtained organic layer was successively washed with 5 N hydrochloric acid (3 times), water (4 times)
- dry with materialThe resultant product was then dried over anhydrous sodium sulfate
- customAfter removing the drying agent
- filtrationby filtration
- concentrationthe organic layer was concentrated under a reduced pressure
- additionHexane was added to the residue
- filtrationthe precipitate was then collected by filtration
Sources & evidence
- ORD record
- ord-3619f1c738e14c6c93b05fc3e701d4ca
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538123B2
Reaction notes
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